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There are a few good ways to get this challenge completed.
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Go to a busy street like the main strip downtown and you should hit level 8 streaking- the longest you can streak at one time easily. You don’t need to do this, but it keeps the time going so you don’t have to keep restarting. The character will then have a certain amount of time to shock a number of people. When you are nekkid, head streetside and double tap down on the D-Pad to initiate the streaking run. To streak around Steelport, you need to hit a crib or store and remove all your clothing- although shoes and boots are allowed for streaking.
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